1. Field of the Invention
The present invention relates to hydroxycucurbituril derivatives, their preparation methods and uses, and more particularly, hydroxycucurbituril derivatives which can easily introduce substituents according to uses, their preparation methods and uses.
2. Description of the Related Art
Cucurbituril was first reported by R. Behrend, E. Meyer and F. Rusche in 1905. According to their report (Liebigs Ann. Chem. 1905, 339, 1.), the condensation of glycoluril and excess formaldehyde in the presence of hydrochloric acid (HCl) produces an amorphous solid. Dissolution of the solid in hot concentrated sulfuric acid, dilution of the solution with water followed by slow cooling of the solution to room temperature produces a crystalline material. They wrongly characterized this substance as C10H11N7O4.2H2O without discovery of its structure.
In 1981, this substance was rediscovered by Mock and coworkers. They correctly characterized it as a hexameric macrocyclic compound with composition of C36H36N24O12, which was also confirmed by X-ray crystal structure determination (J. Am. Chem. Soc., 1981, 103, 7367). They named it cucurbituril which we from now on refer to as cucurbit[6]uril. Since then an improved preparation procedure for cucurbit[6]uril has been disclosed (DE 196 03 377 A1).
In 2000, Kim and coworkers synthesized novel cucurbit[6]uril homologues thereof, cucurbit[n]uril (n=5, 7, 8) and isolated the same, which were confirmed by X-ray crystal structure determination (J. Am. Chem. Soc., 2000, 122, 540).
WO 00/68232 discloses cucurbit[n]uril having the formula:
wherein n is an integer between 4 and 20.
The cucurbituril derivatives are compounds of substitutent-free glycoluril monomers.
A cucurbituril derivative synthesized from glycoluril having a substituent introduced thereto has been reported (Angew. Chem. Int. Ed. Engl. 1992, 31, 1475). According to this report, decamethylcucurbit[5]uril was synthesized using five dimethanodimethylglycoluril units forming a cyclic structure by the condensation of dimethylglycoluril and formaldehyde.
However, in the cucurbiturils and their derivatives proposed up to now, it is not easy to introduce functional groups thereto by substitution, and thus their applications are limited. Also, in order to produce substituted cucurbituril derivatives, different glycoluril monomers must be synthesized and subjected to cyclization, making their synthetic methods complex.